Trifluoromethanesulfonamide, diphenylphosphoramide and diphenylthiophosphoramide of (R)-(+)-1,1'-binaphthyl-2,2'-diamine as chiral catalyst ligands for the titanium(IV) alkoxide-promoted addition of diethylzinc to aldehydes

Chiral trifluoromethanesulfonamide 4, diphenylphosphoramides 5 and 6, and phenylthiophosphoramide 7 were prepared from the reaction of trifluoromethanesulfonic anhydride, diphenylphosphinic chloride, and diphenylthiophosphinic chloride with (R)-(+)-1,1'-binaphthyl-2, 2'-diamine, respectively. They were used as catalytic chiral ligands in the asymmetric addition reaction of diethylzinc to aldehydes in the presence of titanium(IV) isopropoxide to give the corresponding sec-alcohols with 43-54%, 18-22%, 30-34%, and 52-64% enantiomeric excess, respectively. Copyright 2000 Wiley-Liss, Inc.